WO1997047196A1 - Amelioration de l'efficacite d'herbicides - Google Patents

Amelioration de l'efficacite d'herbicides Download PDF

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Publication number
WO1997047196A1
WO1997047196A1 PCT/FI1997/000373 FI9700373W WO9747196A1 WO 1997047196 A1 WO1997047196 A1 WO 1997047196A1 FI 9700373 W FI9700373 W FI 9700373W WO 9747196 A1 WO9747196 A1 WO 9747196A1
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Prior art keywords
betaine
herbicide
herbicides
effect
combination
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PCT/FI1997/000373
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English (en)
Inventor
Kari Jokinen
Jussi Hautala
Liisa Eronen
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Cultor Corporation
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Application filed by Cultor Corporation filed Critical Cultor Corporation
Priority to US09/202,343 priority Critical patent/US6083876A/en
Priority to BR9709570-2A priority patent/BR9709570A/pt
Priority to EP97926034A priority patent/EP0924984A1/fr
Priority to AU30962/97A priority patent/AU734985B2/en
Publication of WO1997047196A1 publication Critical patent/WO1997047196A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C05—FERTILISERS; MANUFACTURE THEREOF
    • C05G—MIXTURES OF FERTILISERS COVERED INDIVIDUALLY BY DIFFERENT SUBCLASSES OF CLASS C05; MIXTURES OF ONE OR MORE FERTILISERS WITH MATERIALS NOT HAVING A SPECIFIC FERTILISING ACTIVITY, e.g. PESTICIDES, SOIL-CONDITIONERS, WETTING AGENTS; FERTILISERS CHARACTERISED BY THEIR FORM
    • C05G3/00—Mixtures of one or more fertilisers with additives not having a specially fertilising activity
    • C05G3/60—Biocides or preservatives, e.g. disinfectants, pesticides or herbicides; Pest repellants or attractants

Definitions

  • the invention relates to the use of betaine for improving the effect of herbicides. It also relates to a combination of herbicide and betaine, and to a method of controlling weeds by the use of herbicide and betaine.
  • Herbicides have a phytotoxic effect on plants, and so they are used in plant production for controlling weeds or totally inhibiting their growth.
  • Herbicides can be non-selective, which means that they destroy all growth, or selective in part or full, whereby they can be used for inhibiting the growth of weeds of only certain crop plants.
  • Most herbicides used today are selective and they can be applied onto growing crop plants without damaging them.
  • the problem with the use of selective herbicides is that particularly when a weed and a crop plant are of a closely related genus, the weed is usually resistant to herbicides.
  • the selectivity between crop plants and weeds changes with the use of herbicides.
  • the increased use of herbicides has also been observed to make weeds more resistant to herbicides. Insufficient or impaired effect, in turn, has led to a further increase in the amount of herbicides used.
  • Herbicides are also an environmental problem. They are usually synthetic compounds that have a toxic or harmful effect not only on plants but also on animals.
  • the herbicides used in agriculture decompose in the soil mainly by the effect of micro-organisms.
  • the rate of microbiological decomposition of herbicides varies with the structure of the herbicide and the conditions of decomposition. The rate of decomposition can also depend on the amount of herbicide used in such a way that an increase in the amount slows down the decomposition.
  • the herbicides used in agriculture are also spread to surface water and to other water systems, in which they decompose very slowly causing even more severe damage to the environment.
  • the effect of herbicides can be improved by various additives or adjuvants. The best results are achieved with naturally susceptible species, but the effect can sometimes also be extended to resistant species. If the resistance is based, for example, on the thickness of the wax layer and/or weak migration of the herbicide in a plant, an adjuvant added to the mixture may impair the strength of the wax layer e.g. by improving the penetrativeness of herbicide molecules. Adjuvants, however, are synthetic preparations, and they too are a hazard to the environment. Apart from intensifying the phytotoxic effect of herbicides, adjuvants are also phytotoxic as such. As a result of synergism, the harmful effects on both crop plants and the environment increase.
  • the object of the invention is to find a way of improving the effect of herbicides, simultaneously avoiding the use of substances that are toxic or harmful to plants or animals.
  • betaine intensifies the effect of herbicides on weeds.
  • betaine is a natural product produced by certain plants, animals and micro-organisms, and it has no harmful or toxic effect on plants or animals. To the contrary, betaine has been found to reduce the phytotoxicity of herbicides to crop plants.
  • the invention thus relates to the use of betaine for improving the effect of herbicides.
  • the invention also relates to a synergistic composition or combination of betaine and herbicide.
  • the invention relates to a method of improving the effect of herbicide by the use of betaine. Still further, the invention relates to a method of controlling weeds by the use of herbicide and betaine.
  • betaine and herbicide are applied onto plants either at one time or in batches. They can be administered together, or separately but approximately simultaneously.
  • the herbicide and betaine treatment according to the invention is economically advantageous, and the increase in the crop yield is economically profitable and significant, since weed growth can be reduced without adding the amount of herbicide.
  • the treatment does not cause significantly more work, since it may be performed together with other sprayings of fertilisers or pesticides, and it does not require any new investments in machinery, equipment or space.
  • betaine is a non-toxic natural product with no harmful effects on the environment or the quality of the crop.
  • betaine is a stable substance that remains in plant cells and thereby has a long-standing effect.
  • Betaines are fully N-methylated amino acids. Betaines are natural products that have an important function in both plant and animal metabolism.
  • One of the most common betaines is a glycine derivative in which three methyl groups are bonded to the nitrogen atom of the glycine molecule. This betaine compound is usually called betaine, glycinebetaine or trimethylglycine, and it has the following structural formula:
  • betaines include, for example, alaninebetaine, prolinebetaine and histidinebetaine.
  • a detailed description of betaines is given by R.G. Wyn Jones and R. Storey in The Physiology and Biochemistry of Drought Resistance in Plants, ed. L.G. Paleg and D. Aspinall, Academic Press, Sydney, Australia, 1981 , which is incorporated herein by reference.
  • Betaine thus has a bipolar structure and it contains several chemically reactive methyl groups, which it can donate in enzyme-catalysed reactions. Most organisms are able to synthesise small quantities of betaine e.g. for the methyl function, but they are not able to produce and store large quantities of betaine.
  • the best known organisms that accumulate betaine are plants of the genus Chenopodiaceae, such as sugar beet, and some microbes, and marine invertebrates. Probably the main reason for these organisms to store betaine is that betaine functions as an osmolyte and thereby protects the cells from the effects of osmotic stress.
  • betaine is well compatible with enzymes, and so the betaine content in the cells and cell organelles can be high without that it impairs metabolism. Betaine has also been observed to stabilise the operation of macromolecules in cell membranes: it improves the heat, ion and drought resistance. At cell level, betaine has been observed to have a plant-protecting effect particularly under stress conditions.
  • the literature of the field contains reports, for example, on the use of betaine as a substance prolonging the shelf life of plants and improving the freeze and drought resistance of growing plants. To enhance growth, betaine has also been added to fertilisers. For example, Japanese patent application JP 63-31800, Laid-open No.
  • I-208386 is directed to a growth-enhancing fertiliser to which betaine has been added.
  • Fertilisers mentioned in the JP application include common mixtures of inorganic substances, containing, for example, urea, calcium superphosphate, ammonium phosphate, potassium sulphate, potassium nitrate, magnesium sulphate and/or ammonium sulphate, to which betaine is added.
  • the fertiliser can be used for improving a seed germination rate and intensifying plant growth, which improves the yield and shortens the period of growth.
  • Herbicides are not mentioned or described in the publication, and neither is the effect of betaine on the effect of herbicides.
  • betaine is used as an additive in animal feed or fodder, a similar osmolytically protecting effect is achieved as in plants.
  • the use of betaine as an additive in animal feed also significantly improves animal performance. For example, it has been observed that betaine enhances bowel movement, and adds to feed intake and animal growth. Betaine has also been observed to lower the body fat, for example, in fish, chicken and pig. Further, betaine has been reported to have pharmacological effects. For example, prolinebetaine has been reported to inhibit osteomalacia in chicken, and glycinebetaine has been reported to inhibit harmful effects of coccidiosis in broiler.
  • Betaine can be obtained, for example, from sugar beet by chromatographic methods. Betaine is commercially available from Cultor Oy, Finnsugar Byproducts, as a crystalline anhydrous betaine product. Other betaine products, such as betainemonohydrate, betainehydrochloride and betaine-containing raw solutions, are also commercially available and can be used in the way described in the current invention.
  • betaine is thus used with herbicides to improve their effect.
  • Preferred betaines are glycine betaine and its analogues, i.e. betaines having a relatively small molecule size and derived from natural amino acids, e.g. alanine betaine and proline betaine.
  • the most preferred betaine to be used in accordance with the current invention is glycine betaine.
  • the combined herbicide and betaine treatment according to the invention is suited both for plants that do not normally store betaine in their cells and for plants that can even normally store betaine in the cells.
  • any compound with a herbicidal effect can be used as a herbicide.
  • Herbicides are divided on the basis of their absorption charac ⁇ teristics into leaf herbicides, which are absorbed into plants mainly through leaves, and soil herbicides, which are absorbed into plants mainly through roots. Further, herbicides can be divided into those which act by contact, i.e. destroy only the parts of a plant that they come into immediate contact with, and those which act internally, i.e. migrate to different parts of plant by internal stream flow. With regard to their chemical structure, herbicides are very different. The first herbicides were inorganic compounds that had a non- selective effect, i.e. they were harmful to all plants.
  • herbicides examples are, for example, copper sulphate and certain borates, such as sodium metaborate and disodium octaborate.
  • Most herbicides used today are organic compounds, such as haloalkane acids, phenoxyalkane acids, aromatic acids, amides, nitriles, anilides, nitrophenols, nitrophenyl ethers, carbamates, phenylurea compounds, heterocyclic nitrogen compounds, e.g. triazines, pyridines, pyridazines and pyrimidines, organoarsenic compounds, organophoshorous compounds, sulphonylurea compounds, or imidazolinones.
  • Herbicides are described, for example, in Progress in Pesticide Biochemistry and Toxicology, Vol. 6, Herbicides, ed. D.H. Hutson and T.R. Roberts, John Wiley & Sons, 1987, and Kasvins ⁇ ojeluseuran julkaisuja No. 81, 1990, "Rikkakasvien kemiallinen torjunta, Herbisidit ja niiden kaytt ⁇ " by Jaakko Mukula and Jukka Salonen, which are incorporated herein by reference.
  • Herbicides useful in the invention thus include, but not exclusively, e.g. commonly used heterocyclic nitrogen compounds, such as triazines; other heterocyclic compounds, such as paraquat; organoarsenic compounds; organophosphorous compounds, such as glyphosate and gluphosinate; phenylurea compounds; and sulphonylurea compounds, such as primi- sulphurone, sulphosulphurone, azimsulphurone and ethoxysulphurone.
  • heterocyclic nitrogen compounds such as triazines
  • other heterocyclic compounds such as paraquat
  • organoarsenic compounds such as paraquat
  • organophosphorous compounds such as glyphosate and gluphosinate
  • phenylurea compounds phenylurea compounds
  • sulphonylurea compounds such as primi- sulphurone, sulphosulphurone, azimsulphurone and ethoxysulphurone.
  • preferable substances in sugar beet cultivation include triazines, particularly 4-amino-4,5-dihydro-3-methyl-3- methyl-6-phenyl-1,2,4-triazin-5-one, i.e. metamitrone; other heterocyclic nitrogen compounds, such as (+-)-2-ethoxy-2,3-dihydro-3,3-dimethyl- benzofuran-5-ylmethanesulphonate, i.e. ethofumesate; carbamoylphenyl- carbamates, such as methyl-3-(3-methylcarbaniloyloxy)carbanilate, i.e.
  • Herbicides preferable in rice cultivation include, for example, sulphonylurea compounds, which are also effective herbicides against weeds of cereals, soybean, potato and cotton.
  • Glyphosate which is a total herbicide, is well- suited for cultivation of cereals, and varieties of maize, soybean and cotton made resistant e.g. by gene transfer technology.
  • Gluphosinate is also preferred because of its high rate of decomposition and low toxicity to animals.
  • pyrithiobacsodium used after emergence, as well as trifluraline, pendimethaline, diurone, fluomethurone, cycloxydime, setoxydime, and fluazifop-P-butyl
  • preferred herbicides include oxyacetamides, which are effective, for example, in controlling weeds of cereals, soybean, potato and cotton.
  • betaine is triazines, glyphosate, and sulphonylurea compounds.
  • betaine can be added to the herbicide or herbicide mixture during the use, e.g. by adding betaine to the tank-mix. It is also possible to use a combination of betaine and herbicide, e.g. in the form of a commercially available (ready-for-use) product. Alternatively, herbicide and betaine can be applied onto the object separately but approximately simultaneously. The order of application is then irrelevant: betaine can be added either before or after the herbicide.
  • the improving, positive effect of betaine on herbicides is a dual effect: betaine both improves the killing effect of the herbicides and reduces the phytotoxic effect of the herbicides on the crop plants.
  • herbicidal mixtures that contain various herbicides.
  • Herbicides are usually not for sale as active ingredients but as preparations, or mixtures.
  • Most herbicide preparations are concentrates, which are either liquid or solid and are to be diluted either with water, an aqueous solution, or an organic solvent, such as oil.
  • Solid, ready-for-use herbicide preparations are sold in the form of dust or powder.
  • the most common herbicide products are EC (emulsion concentrate), SC (suspension concentrate) and WG (granule suspendible in water) preparations.
  • betaine is used in depends on the application. For the purposes of the current invention, betaine can be used in different forms.
  • solid betaine can be used as such, formulated with an adjuvant, or used as a combination with a herbicide product.
  • a betaine solution particularly an aqueous solution, is preferred.
  • Another preferred embodiment is a combination of betaine and herbicide either as a ready-for-use product or as a solid composition that can be converted to a suitable form.
  • the betaine- and herbicide-containing combinations and commercial products according to the invention can be formulated by standard methods. Suspension concentrates, granules or tablets usually contain about
  • herbicidal active ingredients in suspension concentrates, water, oil or a mixture of water and oil is used as a carrier liquid.
  • Adjuvants such as anionic, cationic, non-ionic or ampholytic surfactants, are used for improving dispersibility, suspension stability, wettability, penetration and translocation, for emulsifying oil in the actual concentrate, and for effecting miscibility and suspension/emulsion stability of the preparation in a ready-for-use dilution.
  • the preparations can also contain other adjuvants, such as carriers and/or deflocculating agents miscible and/or soluble in water, i.e.
  • kaolin for example kaolin; lignin compounds; anti-foaming agents; thickening agents, such as cellulose derivatives; anti-freezing agents, such as propyleneglycol; organic solvents, such as kerosene; and colouring agents.
  • preservatives such as formaline, can be used, particularly if the preparation contains organic suspending and thickening agents. If necessary, the acidity of the suspension concentrate can be adjusted.
  • inert inorganic e.g. silica, salts
  • organic e.g. cellulose, polyacrylates, urea
  • other pesticides or nutrients can also be included in the formulates.
  • the herbicidal active ingredients of the formulates are preferably ground to a particulate form, i.e. have a particle size of less than 10 ⁇ m, preferably from 1 to 3 ⁇ m. They are ground, for example, dry in an air jet mill, or as a suspension in a bead mill.
  • Suspension concentrates can be formulated, for example, in a reactor by efficient mixing, and granules or tablets can be prepared by previously known methods, for example, by disc granulation, spray drying, fluidized-bed granulation, mixing granulation by a vertical mixer or a paddle mixer, or by extrusion, compacting, centrifugal, jet layer, or spraying/cooling granulation.
  • the betaine can be mixed with a liquid phase.
  • liquid betaine can be absorbed into the carriers and solid betaine can be incorporated directly into the granule/tablet mass.
  • betaine can be present as separate granules or be included in the same granules as the herbicidal active ingredients.
  • any method suitable for the purpose can be used.
  • Compounds can be applied to either soil or plants, either separately or together with other plant-protecting substances, pesticides or nutrients, such as anti-fungal agents, and urea or micron utrients.
  • a common way of applying herbicides is spraying, whereby they are applied either to soil or to leaves, stems or roots of the plants.
  • Another commonly used method is to apply herbicides to the leaves or stems of weeds with suitable spreading devices or spray guns.
  • the herbicide can be applied e.g. as powder as well as as a spray. After the application, the herbicide is either mixed with soil or allowed to absorb into the ground with rain water.
  • the preferred method of applying betaine and any other substances is to spray them onto the leaves of a plant: a more immediate effect is achieved by this method than by methods directed to roots.
  • Even the time of a treatment according to the invention may vary: the treatment can be performed either before sowing, or before or after the emergence.
  • the suitable time is defined by criteria commonly used in the field, taking notice of e.g. the crop plant, the herbicides used, and the cultivation conditions.
  • the substances are administered to the plants either at one time or in batches. It is considered preferable to administer the substances at one time and to perform the treatment at an early stage of growth.
  • the treatment can be repeated several times, if desired.
  • Betaine is used in a quantity sufficient for achieving the desired effect, i.e. for making the herbicide more effective.
  • the amount used naturally varies with the method, time and object.
  • a suitable quantity used with or added to herbicide is thus, for example, about 0.010 to 10 kg/ha plants.
  • the quantity is preferably, for example, about 0.1 to 6 kg/ha, more preferably 0.2 to 4 kg/ha, still more preferably 0.5 to 2 kg/ha, and most preferably about 1 kg/ha.
  • the quantity of betaine can thus vary considerably, and so the quantities given must be understood as being only suggestive. All quantities that operate in the manner described herein thus fall within the scope of the invention.
  • treatment 2 To study the effect of betaine, the third section was treated in the same way as the comparative area, except that in the first and second stages, 2kg/ha glycinebetaine per stage was added to the herbicide mixture.
  • the experiment including betaine is treatment 3.
  • Table 1a shows the total number of weeds excluding redroot pigweed.
  • the results after the first treatment are shown in Table 2a (date of estimation: 14 June in Karkka and 8 June in Rapi), and after the second treatment in Table 2b (date of estimation: 29 June in Karkka and 20 June in Rapi).
  • Chenopodium spp. Chenopodium album, rubrum, glaucum one of Chenopodium spp. Chenopodium album, rubrum, glaucum (one of Chenopodium spp. Chenopodium album, rubrum, glaucum (one of Chenopodium spp. Chenopodium album, rubrum, glaucum (one of Chenopodium spp. Chenopodium album, rubrum, glaucum (one
  • Betaine particularly effectively improved the effect of herbicides on weeds that are usually difficult to control, such as goosefoots (Chenopodium sp.), mayweeds (Tripleurospermum sp.), knotgrass (Polygonum aviculare), and grass.
  • the addition of betaine was not observed to have any harmful effects.
  • EXAMPLE 2 The effect of betaine on the effect of two small-dose herbicides on the market was studied.
  • the herbicides were Logran 20 WG, Ciba-Geigy, comprising 200 g/kg of triasulphurone as an active ingredient; and Ratio, Ciba- Geigy, comprising 500 g/kg of methyltiphensulphurone and 250 g/kg of methyltribenurone as active ingredients. Both preparations have been registered to be sprayed together with an adhesive agent (Citowet or Sito+). To find out the difference in the effect, the recommended quantity of Logran was halved (0.01 kg/ha); Ratio was used in the smallest quantity recommended (0.007 kg/ha).
  • Betaine was used in a dose of 0.01 kg/ha, 0.5 kg/ha, 0.1 kg/ha and 2 kg/ha. In addition, there was an untreated control area. The treatments are presented in Table 5a. The sprayings were performed with a portable propane-operated van der Weij type patch sprayer using 200l/ha of water.
  • the tests were performed as field tests in two different locations: at Jokioinen (test 1 ) and Ylistaro (test 2).
  • the cultivated plant was barley. The tests were performed in random order within blocks, the gross area of an experimental plot was 3x9 m, and the tests were replicated four times.
  • test 1 barley was sown on 22 May 1996, and the harvest was gathered on 3 Sept. 1996.
  • the soil was heavy clay, and 315 kg/ha (N-P-K 26-2-3) of fertiliser was used.
  • test (2) barley was sown on 14 May 1996 and the harvest was gathered on 4 Sept. 1996.
  • the soil was mud, and 500 kg/ha (N-P-K 20-2-12) of fertiliser was used.
  • the number of weeds was counted and the dry weight was weighed five weeks after the spraying.
  • the number of dicotyledonous weeds in test 1 was 279 per m 2 , and their dry weight was 27.5 g/m 2 .
  • the proportion of hemp nettle and goosefoot in the total amount of weeds was 62%.
  • test 2 the number of weeds was smaller, 104 per m 2 , and their dry weight was 10.0 g/m 2 .
  • Tables 6a to 6c, and 7a and 7b The results of tests 1 and 2 are shown in Tables 6a to 6c, and 7a and 7b, respectively.
  • a summary of the results obtained in the tests is presented graphically in figs. 1 to 3, in which figs. 1a and 1b illustrate the effect of betaine and herbicide treatments on the relative number and weight of dicotyledonous weeds, respectively, and figs.
  • betaine improved the effect of herbicide on the number of weeds by about 7% and on the dry weight by about 3%.
  • herbicide Logran or Ratio
  • adhesive agent Sito+
  • betaine improved the effect of the herbicide on violet, goosefoot, forget-me-not, and black bindweed.
  • betaine notably reduced the phytotoxicity of the herbicide preparations.
  • Example 2 The test described in example 2 was repeated using the same herbicides, Logran 20 WG, Ciba-Geigy, and Ratio, Du Pont. The difference from the experiment of example 2 was that the cultivated plant was oat (Yty).
  • test 3 The test was performed as a field test at Jokioinen (test 3) in the same period of growth and in the same way as described in example 2. Oat was sown on 23 May 1996, and the harvest was gathered on 11 Sept. 1996. The soil was heavy clay, and 320 kg/ha (N-P-K 26-2-3) of fertiliser was used. The oat comprised a large number of weeds (over 500 per m 2 ); heavy rainfall delayed the sprayings, which were conducted late, i.e. on 28 June, 1996, by which time oat straw had already started to grow. The treatments are shown in Table 8. TABLE 8. Treatments of oat
  • a betaine dose of 2.0 kg/ha improved the total effect on weeds by up to 24%.
  • the greatest betaine dose of 2.0 kg/ha gave the best results in respect of both weed control and oat yield.
  • the effects on the dry weight of weeds (22 Aug. 1996) are shown in numbers in Table 9 and graphically in Fig. 4.

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Abstract

L'invention porte sur l'utilisation de bétaïne aux fins d'améliorer l'efficacité d'herbicides, ainsi que sur une combinaison utile pour lutter contre les mauvaises herbes et qui, en dehors de l'herbicide, comprend de la bétaïne ainsi qu'éventuellement des adjuvants et additifs classiques. En outre, l'invention concerne un procédé de lutte contre les mauvaises herbes à l'aide d'un herbicide et de bétaïne.
PCT/FI1997/000373 1996-06-14 1997-06-12 Amelioration de l'efficacite d'herbicides WO1997047196A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US09/202,343 US6083876A (en) 1996-06-14 1997-06-12 Effect of herbicides
BR9709570-2A BR9709570A (pt) 1996-06-14 1997-06-12 Melhoramentos no efeito de herbicidas
EP97926034A EP0924984A1 (fr) 1996-06-14 1997-06-12 Amelioration de l'efficacite d'herbicides
AU30962/97A AU734985B2 (en) 1996-06-14 1997-06-12 Improvement in the effect of herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FI962499 1996-06-14
FI962499A FI104533B (fi) 1996-06-14 1996-06-14 Herbisidien tehon parantaminen

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WO1997047196A1 true WO1997047196A1 (fr) 1997-12-18

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AU (1) AU734985B2 (fr)
BR (1) BR9709570A (fr)
CA (1) CA2258145A1 (fr)
FI (1) FI104533B (fr)
WO (1) WO1997047196A1 (fr)

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WO2004095926A2 (fr) * 2003-04-28 2004-11-11 Monsanto Technology, Llc Traitement de plantes et materiaux de propagation de plantes avec un antioxydant pour l'amelioration de la sante de plantes et/ou l'accroissement de rendement
EP1541023A3 (fr) * 2003-12-10 2006-05-10 Goldschmidt GmbH Combinaison ayant une activité biocide pour des applications agricoles
WO2019178663A1 (fr) * 2018-03-23 2019-09-26 Fernandes Ilton Jhonne Alves Herbicide biologique biodégradable

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US9675080B2 (en) * 2009-03-20 2017-06-13 Verdesian Life Sciences U.S., Llc Methods for delaying maturity of crops
US9290442B2 (en) 2013-03-14 2016-03-22 Los Alamos National Security, Llc Preparation of 4-amino-2,4-dioxobutanoic acid
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US6083876A (en) 2000-07-04
FI104533B (fi) 2000-02-29
CA2258145A1 (fr) 1997-12-18
EP0924984A1 (fr) 1999-06-30
FI962499A0 (fi) 1996-06-14
AU3096297A (en) 1998-01-07
AU734985B2 (en) 2001-06-28
BR9709570A (pt) 1999-09-28
FI962499A (fi) 1997-12-15

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